Method for releasing aldehyde or ketone

ABSTRACT

The invention relates to a method for releasing an aldehyde or ketone of formula (2) by allowing a hydrolase to act on a compound of formula (1). The compound of formula (1) is used as a flavor or fragrance precursor. In formula (1), each of R 1 , R 2  and R 3  independently represents a hydrogen atom, an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, an alkenyl group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent. R 1  and R 2  or R 1  and R 3  may form a ring. Ar represents an aryl group which may have a substituent. In formula (2), R 1 , R 2  and R 3  have the same definitions as those in formula (1). R 1  and R 2  or R 1  and R 3  may form a ring:

TECHNICAL FIELD

The present invention relates to a flavor or fragrance precursor whichreleases an aldehyde or a ketone by the action of hydrolase, a techniquefor lasting lingering fragrance, and a deodorization technique ofreleasing, as a deodorizing component, an aldehyde or a ketone by theaction of a microorganism and mitigating the odor caused bymicroorganisms.

BACKGROUND ART

In recent years, with an increased consumer's interest in fragrance, ademand for fragrance at the time of using a product ranges widely. Withrespect to the needs for improvements in the fragrance substantivity,compounded flavors or fragrances or flavor or fragrance capsules, inwhich a lot of a last note component with low volatility is blended, areused in general.

In addition, as a fragrance substantivity-enhancing agent, for example,a fixative such as p-menthane-3,8-diol (Patent Literature 1) and3-(menthoxy)-1,2-propanediol (Patent Literature 2) has been proposed.

On the other hand, in recent years, due to an increased interest inhygiene, many people have become sensitized to “a scent in living space”and consequently, even a scent that they have been heretofore not awareof in life often assumes a target malodor. Among these, malodorsassociated with human body or laundry are known to be mainly caused bymicroorganisms. As the method for deodorizing these malodors, there areused, for example, a method of suppressing proliferation ofmicroorganisms by using an antimicrobial (Patent Literature 3), and amethod of alleviating unpleasant sensation by using a flavor orfragrance (Patent Literatures 4 and 5).

Furthermore, the flavor or fragrance is highly useful in that not onlyan offensive odor is reduced but also a malodor can be changed to apleasant scent. A flavor or fragrance component such as aldehydes orketones has an aromaticity and is expected to provide a sensorydeodorization effect. Among flavor or fragrance components,particularly, aldehydes have not only a sensuous deodorization effectbut also further have a chemical deodorization effect (Patent Literature6) and therefore, these are expected to provide a higher deodorizingeffect.

RELATED ART Patent Literature

Patent Literature 1: JP-A-4-337395

Patent Literature 2: JP-A-2002-88391

Patent Literature 3: JP-A-2009-46442

Patent Literature 4: JP-A-2004-315502

Patent Literature 5: JP-A-11-286428

Patent Literature 6: JP-A-2001-303090

SUMMARY OF THE INVENTION Problems that the Invention is to Solve

However, when a compounded flavor or fragrance is used in a product, forexample, after clothing or hair is cleaned with a cleaner, most offlavor or fragrance components are washed away into water together withcleaning components such as surfactant and therefore, only a very smallamount of flavor or fragrance components remain in clothing or hair.

In addition, many flavor or fragrance components are volatilized indrying step, as a result, the lingering fragrance intensity is reduced.Furthermore, since the lingering fragrance component isdisproportionated to a flavor or fragrance component having an extremelylow volatility, the taste is readily deteriorated, and an unpleasanttaste may be felt.

In the case of using a flavor or fragrance capsule, the lingeringfragrance may be enhanced, but there is a problem that stabilization ina product is difficult and the application field is limited; and since afragrance is not released unless the capsule is physically broken, afragrance may be emitted when the lingering fragrance is not needed, ora fragrance is not given when the lingering fragrance is needed, causinga gap between the need for a fragrance and the timing of emitting afragrance from the capsule.

In addition, when a fixative is used as a fragrancesubstantivity-enhancing agent together with a compounded flavor orfragrance, the lingering fragrance property may be somewhat enhanced,but fully satisfactory substantivity of lingering fragrance has not beenobtained.

Furthermore, since the lingering fragrance component is stilldisproportionated to a low-volatile component, these techniques did notlead to an improvement in the fragrance quality of the lingeringfragrance, and a technique for lasting fragrance to allow a flavor orfragrance with fresher feeling to last is demanded.

On the other hand, in the case of using an antimicrobial in a personalcare product such as a deodorant agent, not only bacteria causing amalodor but also bacteria useful on skin are killed, and the skin florabalance may be lost. The indigenous skin bacteria also fulfill the roleof keeping the pH weakly acidic and preventing skin infections and inview of maintaining the health of the skin, frequent use of anantimicrobial is not necessarily favorable.

In addition, after washing clothing or hair with a cleaner containing anantimicrobial, most of the antimicrobial components are washed away intowater together with cleaning components such as surfactant andtherefore, only a very small amount of antimicrobial components remainin clothing or hair. In order to kill the malodor-causing bacteria tosuch an extent that offensive odor is not sensed, a large amount ofantimicrobial or an antimicrobial having a high bactericidal effectneeds to be used, and this may raise the concern of adverse effect onhuman body or environment and cause a rise in the cost.

Furthermore, in the case of using a flavor or fragrance as a sensorydeodorant, this is effective in the short term, but since the fragranceintensity weakens due to volatilization of a flavor or fragrancecomponent with time, the deodorizing effect does not last. Moreover, asfor the malodor caused by microorganisms, the odor intensity andunpleasant sensation are strengthened along with progress ofproliferation of microorganisms, and it is likely that when the consumertruly needs the deodorizing effect, a sufficient deodorizing effect isnot obtained due to weak lingering fragrance intensity of the flavor orfragrance. The lingering fragrance property may be increased to enhancethe sustained deodorization, but since this leads to inclination to aflavor or fragrance component having an extremely low volatility in theflavor or fragrance composition, the taste is readily deteriorated, anddiscomfort may be felt.

It may also be conceived to use a flavor or fragrance having a highfragrance intensity or extremely raise the perfuming amount, but, forexample, at the start of use of a deodorant product, during use of abody cleaner, or during drying of clothing, the flavor or fragrancesmells too strong, and the user may be offended.

Accordingly, for the malodor caused by microorganisms, a deodorizationtechnique capable of exerting a deodorizing effect at the same timing assufficient proliferation of microorganisms and generation of malodor isdemanded.

The present invention has been made in consideration of theseconventional circumstances, and an object of the present invention is todevelop a technique enabling a lingering fragrance having fresh feelingto last.

Another object of the present invention is to develop a deodorizingmethod and a deodorant, which can exert a deodorizing effect on themalodor caused by microorganisms at the same timing as sufficientproliferation of microorganisms and generation of malodor.

Means for Solving the Problems

As a result of intensive studies to attain the objects above, thepresent inventors have found that when a compound having a specificstructure releases an aromatic aldehyde or ketone by the action of ahydrolase, the substantivity of lingering fragrance having fresh feelingis increased.

In addition, the present inventors have found that when a compoundhaving a specific structure releases an aldehyde or a ketone by theaction of a microorganism, the odor caused by microorganisms isalleviated.

More specifically, the present invention relates to the following [1] to[17].

[1] A method for releasing an aldehyde or ketone represented by formula(2) by allowing a hydrolase to act on a compound represented by formula(1), in which the compound represented by formula (1) is used as aflavor or fragrance precursor:

(in formula (1), each of R¹, R² and R³ independently represents ahydrogen atom, an alkyl group which may have a substituent, a cycloalkylgroup which may have a substituent, an alkenyl group which may have asubstituent, an aryl group which may have a substituent, or an aralkylgroup which may have a substituent, R¹ and R² or R¹ and R³ may form aring, and Ar represents an aryl group which may have a substituent),and:

(in formula (2), R¹, R² and R³ have the same definitions as those informula (1), and R¹ and R² or R¹ and R³ may form a ring).

[2] The method for releasing an aldehyde or a ketone according to [1],wherein the hydrolase is lipase.

[3] The method for releasing an aldehyde or a ketone according to [1] or[2], wherein each of R¹, R² and R³ is independently a hydrogen atom, analkyl group having 1 to 13 carbon atoms, which may have a substituent,or an alkenyl group having 2 to 13 carbon atoms, which may have asubstituent.

[4] A deodorizing method including allowing a microorganism to act on acompound represented by formula (1) to release, as a deodorizingcomponent, an aldehyde or ketone represented by formula (2) andmitigating an odor caused by microorganism:

(in formula (1), each of R¹, R² and R³ independently represents ahydrogen atom, an alkyl group which may have a substituent, a cycloalkylgroup which may have a substituent, an alkenyl group which may have asubstituent, an aryl group which may have a substituent, or an aralkylgroup which may have a substituent, R¹ and R² or R¹ and R³ may form aring, and Ar represents an aryl group which may have a substituent),and:

(in formula (2), R¹, R² and R³ have the same definitions as those informula (1), and R¹ and R² or R¹ and R³ may form a ring).

[5] The deodorizing method according to [4], wherein the microorganismis at least one selected from the group consisting of Staphylococcusbacteria, Corynebacterium bacteria, Propionibacterium bacteria,Pseudomonas bacteria, Bacillus bacteria, Moraxella bacteria, andMalassezia fungi.

[6] The deodorizing method according to [4] or [5], wherein each of R¹,R² and R³ is independently a hydrogen atom, an alkyl group having 1 to13 carbon atoms, which may have a substituent, or an alkenyl grouphaving 2 to 13 carbon atoms, which may have a substituent.

[7] A compound represented by formula (3):

(in formula (3), a wavy line represents either one of E and Z geometricisomers or a mixture thereof).

[8] A compound represented by formula (4):

(in formula (4), a wavy line represents either one of E and Z geometricisomers or a mixture thereof).

[9] A flavor or fragrance composition containing a compound representedby formula (1):

(in formula (1), each of R¹, R² and R³ independently represents ahydrogen atom, an alkyl group which may have a substituent, a cycloalkylgroup which may have a substituent, an alkenyl group which may have asubstituent, an aryl group which may have a substituent, or an aralkylgroup which may have a substituent, R¹ and R² or R¹ and R³ may form aring, and Ar represents an aryl group which may have a substituent).

[10] The flavor or fragrance composition according to [9], wherein eachof R¹, R² and R³ is independently a hydrogen atom, an alkyl group having1 to 13 carbon atoms, which may have a substituent, or an alkenyl grouphaving 2 to 13 carbon atoms, which may have a substituent.

[11] A flavor or fragrance composition containing a compound representedby formula (3):

(in formula (3), a wavy line represents either one of E and Z geometricisomers or a mixture thereof).

[12] A flavor or fragrance composition containing a compound representedby formula (4):

(in formula (4), a wavy line represents either one of E and Z geometricisomers or a mixture thereof).

[13] An aroma product, a laundry care product, a hair care product, acosmetic, a cleaner or a deodorant, containing a compound represented byformula (1):

(in formula (1), each of R¹, R² and R³ independently represents ahydrogen atom, an alkyl group which may have a substituent, a cycloalkylgroup which may have a substituent, an alkenyl group which may have asubstituent, an aryl group which may have a substituent, or an aralkylgroup which may have a substituent, R¹ and R² or R¹ and R³ may form aring, and Ar represents an aryl group which may have a substituent).

[14] The aroma product, laundry care product, hair care product,cosmetic, cleaner or deodorant according to [13], wherein each of R¹, R²and R³ is independently a hydrogen atom, an alkyl group having 1 to 13carbon atoms, which may have a substituent, or an alkenyl group having 2to 13 carbon atoms, which may have a substituent.

[15] An aroma product, a laundry care product, a hair care product, acosmetic, a cleaner or a deodorant, containing a compound represented byformula (3):

(in formula (3), a wavy line represents either one of E and Z geometricisomers or a mixture thereof).

[16] An aroma product, a laundry care product, a hair care product, acosmetic, a cleaner or a deodorant, containing a compound represented byformula (4):

(in formula (4), a wavy line represents either one of E and Z geometricisomers or a mixture thereof).

[17] An aroma product, a laundry care product, a hair care product, acosmetic, a cleaner or a deodorant, containing the flavor or fragrancecomposition according to any one of [9] to [12].

Advantage of the Invention

In the present invention, the compound represented by formula (1) canrelease an aldehyde or ketone having aromaticity by the action of ahydrolase and increase the substantivity of a lingering fragrance havingfresh feeling.

In addition, by incorporating the compound represented by formula (1), aflavor or fragrance composition, an aroma product, a laundry careproduct, a hair care product, a cosmetic, or a cleaner, each of whichemits an aroma when allowing a hydrolysate to act thereon and causes alingering fragrance having fresh feeling to last, can be provided.

Furthermore, in the present invention, the compound represented byformula (1) can release an aldehyde or ketone having a deodorizingeffect, represented by formula (2), by the action of a microorganism andmitigate the odor caused by microorganisms.

Moreover, by incorporating the compound represented by formula (1), adeodorant which can emit a deodorizing component when allowing amicroorganism to act thereon and mitigate the offensive odor caused bymicroorganisms, can be provided.

MODE FOR CARRYING OUT THE INVENTION

The present invention is described in detail below.

In the present invention, a compound represented by formula (1) is usedas a flavor or fragrance precursor and by allowing a hydrolysate to actthereon, an aldehyde or a ketone, which is a compound represented byformula (2) as a flavor or fragrance component, can be emitted.

In addition, by allowing a microorganism to act on the compoundrepresented by formula (1), an aldehyde or ketone, which is adeodorizing component represented by formula (2), can be emitted, andthis makes it possible to mitigate the odor caused by microorganisms andperform the deodorization.

[Compound Represented by Formula (1) and Compound Represented by Formula(2)]

The compound represented by formula (1) and the compound represented byformula (2) are described.

Compound Represented by Formula (1):

In formula (1), each of R¹, R² and R³ independently represents ahydrogen atom, an alkyl group which may have a substituent, a cycloalkylgroup which may have a substituent, an alkenyl group which may have asubstituent, an aryl group which may have a substituent, or an aralkylgroup which may have a substituent, R¹ and R² or R¹ and R³ may form aring, and Ar represents an aryl group which may have a substituent.

Compound Represented by Formula (2):

In formula (2), R¹, R² and R³ have the same definitions as those informula (1). R¹ and R² or R¹ and R³ may form a ring.

(Groups Represented by R¹, R² and R³)

The alkyl group, the cycloalkyl group, the alkenyl group, the aryl groupand the aralkyl group, each of which is represented by R¹, R² and R³,are described. Each of these groups may have a substituent.

The alkyl group includes, for example, a straight chain or branchedalkyl group having 1 to 30 carbon atoms, preferably 1 to 13 carbonatoms. Specifically, examples thereof include a methyl group, an ethylgroup, a n-propyl group, an isopropyl group, a n-butyl group, a 2-butylgroup, an isobutyl group, a tert-butyl group, a n-pentyl group, a2-pentyl group, a 3-pentyl group, a tert-pentyl group, a 2-methylbutylgroup, a 3-methylbutyl group, a 2,2-dimethylpropyl group, a1,2-dimethylpropyl group, a n-hexyl group, a 2-hexyl group, a 3-hexylgroup, a 2-methylpentyl group, a 3-methylpentyl group, a 4-methylpentylgroup, a 1,1-dimethylbutyl group, a 1,2-dimethylbutyl group, a1,3-dimethylbutyl group, a 2,2-dimethylbutyl group, a 2,3-dimethylbutylgroup, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a1,1,2-trimethylpropyl group, a 1,2,2-trimethylpropyl group, a1-ethyl-1-methylpropyl group, a 1-ethyl-2-methylpropyl group, a heptylgroup, an octyl group, a 1,5-dimethylhexyl group, a nonyl group, a decylgroup, an undecyl group, a dodecyl group, a tridecyl group, a1,5,9-trimethyldecyl group, a tetradecyl group, a pentadecyl group, ahexadecyl group, a heptadecyl group, an octadecyl group, a nonadecylgroup, an eicosyl group, a heneicosyl group, a docosyl group, etc.

Examples of the cycloalkyl group include a cyclopropyl group, acyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc.

The alkenyl group includes, for example, a straight chain or branchedalkenyl group having 2 to 20 carbon atoms, preferably 2 to 13 carbonatoms, and a cyclic alkenyl group having 3 to 20 carbon atoms,preferably 5 to 10 carbon atoms.

Specifically, examples of the alkenyl group include a vinyl group, a1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenylgroup, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a3-pentenyl group, a 4-pentenyl group, a 1-cyclopentenyl group, a3-cyclopentenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenylgroup, a 4-hexenyl group, a 5-hexenyl group, a 4-methyl-3-pentenylgroup, a 4,8-dimethyl-3,7-nonadienyl group, a 1-cyclohexenyl group, a3-cyclohexenyl group, a 1,5-dimethyl-4-hexenyl group, a1,5-dimethyl-1,4-hexadienyl group, a 1,5,9-trimethyl-4,8-decadienylgroup, etc.

The aryl group includes, for example, an aryl group having 6 to 14carbon atoms. Specifically, examples thereof include a phenyl group, anaphthyl group, an anthryl group, a phenanthryl group, a biphenyl group,etc.

As the aralkyl group, for example, an aralkyl group having 7 to 12carbon atoms is preferred. Specifically, examples thereof include abenzyl group, a 2-phenylethyl group, a 1-phenylpropyl group, etc.

Each of the groups R¹ to R³ other than a hydrogen atom may have asubstituent. Examples of the substituent include an alkenyl group, analkynyl group, an aryl group, an aliphatic heterocyclic group, anaromatic heterocyclic group, an alkoxy group, an alkylenedioxy group, anaryloxy group, an aralkyloxy group, a heteroaryloxy group, an aminogroup, a substituted amino group, a nitro group, a cyano group, analkoxycarbonyl group, a halogen atom, an alkyl halide group, etc.

The alkenyl group as the substituent on R¹ to R³ may be a straight chainor branched alkenyl group and includes, for example, an alkenyl grouphaving 2 to 20 carbon atoms, preferably 2 to 10 carbon atoms, morepreferably 2 to 6 carbon atoms. Specifically, examples thereof include avinyl group, a propenyl group, a 1-butenyl group, a pentenyl group, ahexenyl group, etc.

The alkynyl group as the substituent on R¹ to R³ may be a straight chainor branched alkynyl group and includes, for example, an alkynyl grouphaving 2 to 15 carbon atoms, preferably 2 to 10 carbon atoms, morepreferably 2 to 6 carbon atoms. Specifically, examples thereof includean ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynylgroup, a 3-butynyl group, a pentynyl group, a hexynyl group, etc.

The aryl group as the substituent on R¹ to R³ includes, for example, anaryl group having 6 to 14 carbon atoms. Specifically, examples thereofinclude a phenyl group, a naphthyl group, an anthryl group, aphenanthryl group, a biphenyl group, a tolyl group, a xylyl group, amesityl group, a methoxyphenyl group, a dimethoxyphenyl group, afluorophenyl group, etc.

The aliphatic heterocyclic group as the substituent on R¹ to R³includes, for example, a group having 2 to 14 carbon atoms andcontaining at least one, preferably 1 to 3, hetero atoms such asnitrogen atom, oxygen atom and sulfur atom. Preferably, the aliphaticheterocyclic group includes a 5- or 6-membered monocyclic aliphaticheterocyclic group and a polycyclic or condensed ring aliphaticheterocyclic group.

Specific examples of the aliphatic heterocyclic group include a2-oxo-1-pyrrolidinyl group, a piperidino group, a piperazinyl group, amorpholino group, a tetrahydrofuryl group, a tetrahydropyranyl group, atetrahydrothienyl group, etc.

The aromatic heterocyclic group as the substituent on R¹ to R³ includes,for example, a group having 2 to 15 carbon atoms, preferably 3 to 11carbon atoms, and containing at least one, preferably 1 to 3, heteroatoms such as nitrogen atom, oxygen atom and sulfur atom. Preferably,the aromatic heterocyclic group includes a 5- or 6-membered monocyclicaromatic heterocyclic group and a polycyclic or condensed ring aromaticheterocyclic group.

Specific examples of the aromatic heterocyclic group include a furylgroup, a thienyl group, a pyridyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a pyrazolinyl group, an imidazolylgroup, an oxazolinyl group, a thiazolinyl group, a benzofuryl group, abenzothienyl group, a quinolyl group, an isoquinolyl group, aquinoxalinyl group, a phtharazinyl group, a quinazolinyl group, anaphthylidinyl group, a cinnolinyl group, a benzimidazolyl group, abenzoxazolyl group, a benzothiazolyl group, etc.

The alkoxy group as the substituent on R¹ to R³ includes, for example, astraight chain or branched alkoxy group having 1 to 6 carbon atoms.Specifically, examples thereof include a methoxy group, an ethoxy group,a n-propoxy group, an isopropoxy group, a n-butoxy group, a 2-butoxygroup, an isobutoxy group, a tert-butoxy group, a n-pentyloxy group, a2-methylbutoxy group, a 3-methylbutoxy group, a 2,2-dimethylpropoxygroup, a n-hexyloxy group, a 2-methylpentyloxy group, a3-methylpentyloxy group, a 4-methylpentyloxy group, a 5-methylpentyloxygroup, etc.

The alkylenedioxy group as the substituent on R¹ to R³ includes, forexample, an alkylenedioxy group having 1 to 3 carbon atoms.Specifically, examples thereof include a methylenedioxy group, anethylenedioxy group, a propylenedioxy group, an isopropylidenedioxygroup, etc.

The aryloxy group as the substituent on R¹ to R³ includes, for example,an aryloxy group having 6 to 14 carbon atoms. Specifically, examplesthereof include a phenoxy group, a naphthyloxy group, an anthryloxygroup, etc.

The aralkyloxy group as the substituent group for R¹ to R³ includes, forexample, an aralkyloxy group having 7 to 12 carbon atoms. Specifically,examples thereof include a benzyloxy group, a 2-phenylethoxy group, a1-phenylpropoxy group, a 2-phenylpropoxy group, a 3-phenylpropoxy group,a 1-phenylbutoxy group, a 2-phenylbutoxy group, a 3-phenylbutoxy group,a 4-phenylbutoxy group, a 1-phenylpentyloxy group, a 2-phenylpentyloxygroup, a 3-phenylpentyloxy group, a 4-phenylpentyloxy group, a5-phenylpentyloxy group, a 1-phenylhexyloxy group, a 2-phenylhexyloxygroup, a 3-phenylhexyloxy group, a 4-phenylhexyloxy group, a5-phenylhexyloxy group, a 6-phenylhexyloxy group, etc.

The heteroaryloxy group as the substituent on R¹ to R³ includes, forexample, a heteroaryloxy group having 2 to 14 carbon atoms andcontaining at least one, preferably 1 to 3, hetero atoms such asnitrogen atom, oxygen atom and sulfur atom. Specifically, examplesthereof include a 2-pyridyloxy group, a 2-pyrazyloxy group, a2-pyrimidyloxy group, a 2-quinolyloxy group, etc.

Examples of the substituted amino group as the substituent on R¹ to R³include a mono- or dialkylamino group, such as N-methylamino group,N,N-dimethylamino group, N,N-diethylamino group, N,N-diisopropylaminogroup and N-cyclohexylamino group; a mono- or diarylamino group, such asN-phenylamino group, N,N-diphenylamino group, N-naphthylamino group andN-naphthyl-N-phenylamino group; and a mono- or diaralkylamino group,such as N-benzylamino group and N,N-dibenzylamino group; etc.

The alkoxycarbonyl group as the substituent on R¹ to R³ is preferably,for example, an alkoxycarbonyl group having 1 to 30 carbon atoms.Specifically, examples thereof include a methoxycarbonyl group, anethoxycarbonyl group, a n-propoxycarbonyl group, an isopropoxycarbonylgroup, a n-butoxycarbonyl group, a 2-butoxycarbonyl group, anisobutoxycarbonyl group, a tert-butoxycarbonyl group, an-pentyloxycarbonyl group, a 2-methylbutoxycarbonyl group, a3-methylbutoxycarbonyl group, a 2,2-dimethylpropoxycarbonyl group, an-hexyloxycarbonyl group, a 2-methylpentyloxycarbonyl group, a3-methylpentyloxycarbonyl group, a 4-methylpentyloxycarbonyl group, a5-methylpentyloxycarbonyl group, a cyclopentyloxycarbonyl group, acyclohexyloxycarbonyl group, a dicyclopentylmethoxycarbonyl group, adicyclohexylmethoxycarbonyl group, a tricyclopentylmethoxycarbonylgroup, a tricyclohexylmethoxycarbonyl group, a phenylmethoxycarbonylgroup, a diphenylmethoxycarbonyl group, a triphenylmethoxycarbonylgroup, etc.

Examples of the halogen atom as the substituent on R¹ to R³ include afluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.

The alkyl halide group as the substituent on R¹ to R³ is preferably, forexample, a perhalogenoalkyl group having 1 to 10 carbon atoms.Specifically, examples thereof include a trifluoromethyl group, apentafluoroethyl group, a heptafluoropropyl group, an undecafluoropentylgroup, a heptadecafluorooctyl group, an undecafluorocyclohexyl group, adichloromethyl group, etc.

In the compound represented by formula (1), examples of the ring formedby R¹ and R² or R¹ and R³ include a cyclopentane ring, a cyclohexanering, an indane ring, a tetralin ring, a cyclopentene ring, acyclohexene ring, a cycloheptene ring, an indene ring, adihydronaphthalene ring, an octahydronaphthalene ring, adecahydronaphthalene ring, etc. These rings may be substituted with theabove-described alkyl group or the like.

In the compound represented by formula (2), examples of the ring formedby R¹ and R² or R¹ and R³ include a cyclopentane ring, a cyclohexanering, an indane ring, a tetralin ring, a cyclopentene ring, acyclohexene ring, a cycloheptene ring, an indene ring, adihydronaphthalene ring, an octahydronaphthalene ring, adecahydronaphthalene ring, etc. These rings may be substituted with theabove-described alkyl group or the like.

Among those described above, each of R¹, R² and R³ is preferably ahydrogen atom, an alkyl group having 1 to 13 carbon atoms, which mayhave a substituent group, or an alkenyl group having 2 to 13 carbonatoms, which may have a substituent.

The alkyl group having 1 to 13 carbon atoms, which may have asubstituent, is preferably, for example, a straight chain or branchedalkyl group having 1 to 13 carbon atoms. Specifically, examples thereofinclude a methyl group, an ethyl group, a n-propyl group, an isopropylgroup, a n-butyl group, a 2-butyl group, an isobutyl group, a tert-butylgroup, a n-pentyl group, a 2-pentyl group, a 3-pentyl group, atert-pentyl group, a 2-methylbutyl group, a 3-methylbutyl group, a2,2-dimethylpropyl group, a 1,2-dimethylpropyl group, a n-hexyl group, a2-hexyl group, a 3-hexyl group, a 2-methylpentyl group, a 3-methylpentylgroup, a 4-methylpentyl group, a 1,1-dimethylbutyl group, a1,2-dimethylbutyl group, a 1,3-dimethylbutyl group, a 2,2-dimethylbutylgroup, a 2,3-dimethylbutyl group, a 3,3-dimethylbutyl group, a2-ethylbutyl group, a 1,3,3-trimethylbutyl group, a1,1,2-trimethylpropyl group, a 1,2,2-trimethylpropyl group, a1-ethyl-1-methylpropyl group, a 1-ethyl-2-methylpropyl group, a heptylgroup, an octyl group, a 1,5-dimethylhexyl group, a nonyl group, a decylgroup, an undecyl group, a dodecyl group, a tridecyl group, a1,5,9-trimethyldecyl group, a 4-methylpentyl group, a 1,5-dimethylhexylgroup, etc.

As the alkenyl group having 2 to 13 carbon atoms, which may have asubstituent, for example, a straight chain or branched alkenyl grouphaving 2 to 13 carbon atoms, and a cyclic alkenyl group having 3 to 13carbon atoms, are preferred. Specifically, examples thereof include avinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group,a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenylgroup, a 3-pentenyl group, a 4-pentenyl group, a 1-cyclopentenyl group,a 3-cyclopentenyl group, a 1-hexenyl group, a 2-hexenyl group, a3-hexenyl group, a 4-hexenyl group, a 5-hexenyl group, a4-methyl-3-pentenyl group, a 1-octenyl group, a 2-octenyl group, a4,8-dimethyl-3,7-nonadienyl group, a 1-cyclohexenyl group, a3-cyclohexenyl group, a 4-methyl-3-pentenyl group, a1,5-dimethyl-1,4-hexadienyl group, a 1,5-dimethyl-4-hexenyl group, a1,5,9-trimethyl-4,8-decadienyl group, etc.

As for more preferred examples of R¹, R² and R³, in view of flavor orfragrance and deodorizing effect, each of R¹ and R² is an alkyl grouphaving 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms,or a hydrogen atom, and R³ is a hydrogen atom.

The alkyl group having 1 to 8 carbon atoms is preferably, for example, astraight chain or branched alkyl group having 1 to 8 carbon atoms.Specifically, examples thereof include a methyl group, an ethyl group, an-propyl group, an isopropyl group, a n-butyl group, a 2-butyl group, anisobutyl group, a tert-butyl group, a n-pentyl group, a 2-pentyl group,a 3-pentyl group, a tert-pentyl group, a 2-methylbutyl group, a3-methylbutyl group, a 2,2-dimethylpropyl group, a 1,2-dimethylpropylgroup, a n-hexyl group, a 2-hexyl group, a 3-hexyl group, a2-methylpentyl group, a 3-methylpentyl group, a 4-methylpentyl group, a1,1-dimethylbutyl group, a 1,2-dimethylbutyl group, a 1,3-dimethylbutylgroup, a 2,2-dimethylbutyl group, a 2,3-dimethylbutyl group, a3,3-dimethylbutyl group, a 2-ethylbutyl group, a 1,3,3-trimethylbutylgroup, a 1,1,2-trimethylpropyl group, a 1,2,2-trimethylpropyl group, a1-ethyl-1-methylpropyl group, a 1-ethyl-2-methylpropyl group, a heptylgroup, an octyl group, a 1,5-dimethylhexyl group, a 4-methylpentylgroup, a 1,5-dimethylhexyl group, etc.

As the alkenyl group having 2 to 8 carbon atoms, specifically, examplesthereof include a vinyl group, a 1-propenyl group, a 2-propenyl group, a1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenylgroup, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a1-cyclopentenyl group, a 3-cyclopentenyl group, a 1-hexenyl group, a2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, a 5-hexenylgroup, a 4-methyl-3-pentenyl group, a 1-octenyl group, a 2-octenylgroup, a 1-cyclohexenyl group, a 3-cyclohexenyl group, a4-methyl-3-pentenyl group, a 1,5-dimethyl-1,4-hexadienyl group, a1,5-dimethyl-4-hexenyl group, etc.

In the case of forming a ring by R¹ and R² or R¹ and R³, in view offlavor or fragrance and deodorizing effect, a cyclohexene ring and acyclohexane group are preferred.

The substituent substituted on the cyclohexene ring and cyclohexane ringis preferably an alkyl group having 1 to 3 carbon atoms. Thesubstitution may be a single substitution or a plurality ofsubstitutions.

The alkyl group having 1 to 3 carbon atoms is preferably, for example, astraight chain or branched alkyl group having 1 to 3 carbon atoms.Specifically, examples thereof include a methyl group, an ethyl group,an n-propyl group, an isopropyl group, etc.

(Group Represented by Ar)

The aryl group represented by Ar, which may have a substituent, isdescribed.

The aryl group includes, for example, an aryl group having 6 to 14carbon atoms. Specifically, examples thereof include a phenyl group, anaphthyl group, an anthryl group, a biphenyl group, etc.

Among these, in view of fragrance emission performance and deodorizingeffect, a phenyl group is preferred.

The substituent which may be substituted on the aryl group includes, forexample, an alkyl group having 1 to 8 carbon atoms. Specifically,examples thereof include a methyl group, an ethyl group, a n-propylgroup, an isopropyl group, a n-butyl group, a 2-butyl group, an isobutylgroup, a tert-butyl group, a n-pentyl group, a 2-pentyl group, a3-pentyl group, a tert-pentyl group, a 2-methylbutyl group, a3-methylbutyl group, a 2,2-dimethylpropyl group, a 1,2-dimethylpropylgroup, a n-hexyl group, a 2-hexyl group, a 3-hexyl group, a2-methylpentyl group, a 3-methylpentyl group, a 4-methylpentyl group, a1,1-dimethylbutyl group, a 1,2-dimethylbutyl group, a 1,3-dimethylbutylgroup, a 2,2-dimethylbutyl group, a 2,3-dimethylbutyl group, a3,3-dimethylbutyl group, a 2-ethylbutyl group, a 1,3,3-trimethylbutylgroup, a 1,1,2-trimethylpropyl group, a 1,2,2-trimethylpropyl group, a1-ethyl-1-methylpropyl group, a 1-ethyl-2-methylpropyl group, a heptylgroup, an octyl group, a 1,5-dimethylhexyl group, a 4-methylpentylgroup, a 1,5-dimethylhexyl group, etc. Among these, a methyl group ispreferred.

(Specific Examples of Compound Represented by Formula (1))

Specific examples of the compound represented by formula (1) of thepresent invention include the compounds shown below. In the compoundsillustrated below, the wavy line indicates either one of E and Zgeometric isomers or a mixture thereof.

As for the compound represented by formula (1) of the present invention,particularly, in view of fragrance, fragrance emission performance anddeodorizing effect, a compound represented by the following formula (3)and a compound represented by formula (4) are preferred.

In formula (3), the wavy line indicates either one of E and Z geometricisomers or a mixture thereof.

In formula (4), the wavy line indicates either one of E and Z geometricisomers or a mixture thereof.

(Synthesis Method of Compound Represented by Formula (1))

The compound represented by formula (1) used in the present inventioncan be easily synthesized by a known method.

Out of the compounds represented by formula (1), a production method of3,7-dimethylocta-1,6-dienyl benzoate represented by the followingformula (3) is described.

The compound represented by formula (3) can be synthesized according tothe method described, for example, in Helv. Chim. Acta. 1988, 71,1000-1004. This method can be represented by Scheme 1 below.

As for the synthesis of the compound represented by formula (3), thecompound can be prepared by reacting a mixed solution of citronellal(compound of formula (5)), benzoic anhydride, triethylamine, andbenzoate salt at a temperature ranging from 100 to 150° C. As the usedbenzoate salt, potassium benzoate and sodium benzoate are preferred.

The thus-obtained compound of formula (3) can be isolated in the usualmanner, such as extraction, distillation, recrystallization orchromatography of every sort.

In the compound of formula (3), the wavy line represents either one of Eand Z geometric isomers or a mixture thereof.

(Flavor or Fragrance Component)

The compound represented by formula (1) of the present invention can beused as a flavor or fragrance precursor. By allowing a hydrolysate toact on the compound represented by formula (1), an aldehyde or ketonerepresented by formula (2), which is a flavor or fragrance component,can be released.

The hydrolysate includes lipase, protease, amylase, glycosidase, etc.,and among these, in view of hydrolysis rate, lipase is preferred.

The lipase is not particularly limited and, as long as it is an enzymethat breaks down fat, may be a naturally occurring material or aformulated commercial product.

The aldehyde represented by formula (2), which is a flavor or fragrancecomponent or the later-described deodorizing component, includes astraight chain or branched aliphatic aldehyde having 6 to 13 carbonatoms, trans-2-hexenal, cis-3-hexenal, 2,6-nonadienal, cis-4-decenal,trans-4-decenal, undecylene aldehyde, trans-2-dodecenal,trimethylundecenal, 2,6,10-trimethyl-5,9-undecadienal,2,6-dimethyl-5-heptenal, citral, citronellal, hydroxycitronellal,perillaldehyde, citronellyloxyacetaldehyde,2,4-dimethyl-3-cyclohexenylcarboxyaldehyde,2,4,6-trimethyl-3-cyclohexene-1-carboxyaldehyde,5-methoxy-octahydro-4,7-methano-1H-indene-2-carboxyaldehyde,4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carboxyaldehyde,4-(4-hydroxy-4-methyl-pentyl)-3-cyclohexene-1-carboxyaldehyde,1-methyl-4-(4-methyl-pentyl)-3-cyclohexene-carboxyaldehyde,4-(tricyclo[5.2.1.0^(2,6)]decylidene-8)-butenal,2-methyl-4-(2,6,6-trimethyl-2-cyclohexene-1-yl)-butanal, benzaldehyde,phenylacetoaldehyde, phenylpropylaldehyde, cinnamic aldehyde,α-amylcinnamic aldehyde, α-hexylcinnamic aldehyde, 2-phenylpropanal,anisaldehyde, p-methylphenylacetoaldehyde, cuminaldehyde, cyclamenaldehyde, 3-(p-tert-butylphenyl)-propylaldehyde,p-ethyl-2,2-dimethylhydrocinnamaldehyde,2-methyl-3-(p-methoxyphenyl)-propylaldehyde,4-tert-butyl-α-methylhydrocinnamic aldehyde, salicylaldehyde,heliotropin, 2-methyl-3-(3,4-methylenedioxy-phenyl)-propanal, vanillin,ethylvanillin, methylvanillin, farnesal, dihydrofarnesal,3,5,5-trimethylhexanal, octanal, etc.

The ketone represented by formula (2), which is a flavor or fragrancecomponent or the later-described deodorizing component, includes methylamyl ketone, ethyl amyl ketone, methyl hexyl ketone, methyl nonylketone, methylheptenone, Koavone, camphor, carvone, menthone,isomenthone, pulegone, piperitone, fenchone, geranylacetone, cedrylmethyl ketone, nootkatone, α-ionone, β-ionone, α-methylionone,β-methylionone, α-isomethylionone, β-isomethylionone, allylionone,α-irone, β-irone, γ-irone, α-damascone, β-damascone, δ-damascone,damascenone, α-dinascone, β-dinascone, maltol, ethylmaltol,2,5-dimethyl-4-hydroxyfuranone, 4,5-dimethyl-3-hydroxy-5H-furan-2-one,p-tert-butylcyclohexanone, amylcyclopentanone, heptylcyclopentanone,dihydrojasmone, cis-jasmone,7-methyl-octahydro-1,4-methanonaphthlen-6(2H)-one,4-cyclohexyl-4-methyl-2-pentanone,2,2,5-trimethyl-5-pentylcyclopentanone,4-(1-ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone,6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone,7-acetyl-1,2,3,4,5,6,7,8-octahydro-1,1,6,7-tetramethylnaphthalene,acetophenone, p-methylacetophenone, benzyl acetone,7-methyl-3,4-dihydro-(2H)-1,5-benzodioxepin-3-one, raspberry ketone,anisylacetone, 4-(4-hydroxy-3-methoxyphenyl)-2-butanone, methyl naphthylketone, 4-phenyl-4-methyl-2-pentanone, benzophenone, etc.

(Deodorizing Component)

By allowing a microorganism to act on the compound represented byformula (1), an aldehyde or ketone represented by formula (2), which isa deodorizing component, can be released.

The microorganism that can cause the compound represented by formula (1)of the present invention to release, as a deodorizing component, analdehyde or ketone represented by formula (2) includes Staphylococcusbacteria, Corynebacterium bacteria, Propionibacterium bacteria,Pseudomonas bacteria, Bacillus bacteria, Moraxella bacteria, Malasseziafungi, etc.

Specifically, examples thereof include Staphylococcus aureus,Staphylococcus epidermidis, Corynebacterium xerosis, Propionibacteriumacnes, Pseudomonas aeruginosa, Bacillus subtilis, Moraxella osloensis,Malassezia furfur, etc.

[Flavor or Fragrance Composition]

The compound represented by formula (1) of the present invention can beblended in a flavor or fragrance composition. The compound representedby formula (1) can be used singly or in combination of two or more kindsand can also be appropriately used in combination with a known flavor orfragrance component.

Examples of the known flavor or fragrance component include naturalessential oils, such as lemon oil, orange oil, lime oil, bergamot oil,lavandin oil, lavender oil, geranium oil, rose oil and sandalwood oil;hydrocarbons, such as α-pinene, β-pinene, limonene, p-cymene andthujone; aliphatic alcohols, such as octanol andp-tert-butylcyclohexanol; terpene-based alcohols, such as menthol,citronellol and geraniol; aromatic alcohols, such as benzyl alcohol andphenylethyl alcohol; aliphatic aldehydes; terpene-based aldehydes;aromatic aldehydes; acetals; chain ketones; cyclic ketones, such asdamascone, β-ionone and methylionone; terpene-based ketones, such ascarvone, menthone, isomenthone and camphor; aromatic ketones, such asacetophenone and raspberry ketone; ethers, such as dibenzyl ether;oxides, such as linalool oxide and rose oxide; musks, such ascyclopentadecanolide and cyclohexadecanolide; lactones, such asγ-nonalactone, γ-undecalactone and coumarin; aliphatic esters, such asacetic acid ester and propionic acid ester; aromatic esters, such asbenzoic acid ester and phenylacetic acid ester, etc.

In the flavor or fragrance composition of the present invention, asolvent, for example, ethanol, isopropyl alcohol, ethylene glycol,propylene glycol, dipropylene glycol, butylene glycol, pentylene glycol,hexylene glycol, polyethylene glycol, diethyl phthalate, isopropylmyristate, triethyl citrate, benzyl benzoate, glycerin, triacetin,benzyl alcohol, paraffin, isoparaffin, a rosin ester derivative such asHercolyn, etc., glycol ethers such as 3-methoxy-3-methyl-1-butanol,ethyl carbitol (diethylene glycol monoethyl ether), ethylene glycolmonomethyl ether, propylene glycol monomethyl ether, ethylene glycolmonoethyl ether, dipropylene glycol monomethyl ether, tripropyleneglycol methyl ether, dipropylene glycol dimethyl ether, dipropyleneglycol propyl ether, dipropylene glycol methyl ether acetate,dipropylene glycol butyl ether, etc., a terpene resin such as pinenepolymer, etc., silicones such as cyclic silicone, etc., water, etc., ora fixative may be used.

In addition, a known component, such as higher alcohol, surfactant,antioxidant, ultraviolet absorber, chelating agent, solubilizing agent,stabilizing agent, cooling sensation agent, preservative, antimicrobial,bactericide, fungicide, insecticidal component and coloring matter, maybe further mixed, if desired.

The blending amount of the compound represented by formula (1) of thepresent invention in the flavor or fragrance composition is not strictlyrestricted and can be variously changed according to use of the flavoror fragrance composition. The blending amount of the compoundrepresented by formula (1) of the present invention in the flavor orfragrance composition is preferably from 0.1 to 95.0% by mass, morepreferably from 0.5 to 80.0% by mass.

[Aroma Product, Laundry Care Product, Hair Care Product, Cosmetic, orCleaner]

The compound represented by formula (1) of the present invention can beused, individually or in combination of two or more kinds, for aproduct, such as aroma product, laundry care product, hair care product,cosmetic or cleaner.

Furthermore, in the product, such as aroma product, laundry careproduct, hair care product, cosmetic or cleaner, for the purpose ofletting the fragrance emitted from the product itself, the fragranceduring use of the product, and the lingering fragrance from clothing,hair or skin be more favorable, in addition to the compound representedby formula (1) of the present invention, there may be appropriatelyblended in combination a compounded flavor or fragrance; a powder flavoror fragrance of a known core-shell type, a matrix type using starch orprocessed starch, etc. or a fragrance capsule; a fragrance impregnatedbody prepared by impregnating an inorganic porous material such assilica gel or calcium silicate or an organic porous material such ascelluloses, with a flavor or fragrance; a fragrance inclusion bodyprepared by the inclusion of a flavor or fragrance in α-cyclodextrin,β-cyclodextrin, γ-cyclodextrin, hydroxypropylated β-dextrin, highlybranched cyclic dextrin, etc.; a known flavor or fragrance precursor,pro-fragrance, fragrance precursor, pro-perfume, etc., such as silicicacid ester compound, fatty acid ester compound, acetal compound,hemiacetal compound, Schiff base compound, hemiaminal compound orhydrazone compound, each of which can release a flavor or fragrancecomponent.

Examples of the aroma product include a perfume, eau de cologne, aliquid air freshener, a gel air freshener, a powder air freshener, animpregnated air freshener, a mist spray air freshener, an aerosol sprayair freshener, a plug-in air freshener, an incense stick, a candle, etc.

Examples of the laundry care product include a mist spray for clothing,a spray for clothing, a detergent, a fabric softener, etc.

Examples of the hair care product include a hair shampoo, a hair rinse,a hair conditioner, a hair treatment, a hair tonic, a hair stylingagent, a hair dye, a permanent waving agent, a hair growth agent, a haircologne, etc.

Examples of the cosmetic include a lotion, a milky lotion, a cosmeticcream, a soap, a liquid soap, a facial cleanser, a sunscreen, anantiperspirant, a bath additive, a lipstick, a foundation, etc.

Examples of the cleaner include a toilet cleaner, a toilet bowl cleaner,a glass cleaner, a dishwashing detergent, a washing machine cleaner, adrain cleaner, a bathroom cleaner, etc.

The compound represented by formula (1) of the present inventionreleases a flavor or fragrance component by the action of a hydrolaseand therefore, is particularly useful when a product having blendedtherein the compound represented by formula (1) of the present inventionis used in combination with a product having blended therein ahydrolysate.

The method for using the products in combination is not particularlylimited but includes a method of using a mutual combination of laundrycare products, hair care products, or cosmetics.

As for the mutual combination of laundry care products, examples of themethod include (A) a method of using a combination of a cleaner forclothing, in which a lipase is blended, and a mist spray for clothing, aspray for clothing, a fabric softener, etc., in which the compoundrepresented by formula (1) of the present invention is blended, and (B)a method of using a combination of a cleaner for clothing, in which thecompound represented by formula (1) of the present invention is blended,and a mist spray for clothing, a spray for clothing, a fabric softener,etc., in which a lipase is blended.

As for the mutual combination of hair care products, examples of themethod include (A) a method of using a combination of a shampoo in whicha lipase is blended, and a hair rinse, a hair conditioner, a hairtreatment, a hair styling agent, a hair growth agent, a hair cologne,etc., in which the compound represented by formula (1) of the presentinvention is blended, and (B) a method of using a combination of ashampoo in which the compound represented by formula (1) of the presentinvention is blended, and a hair rinse, a hair conditioner, a hairtreatment, a hair styling agent, a hair growth agent, a hair cologne,etc., in which a lipase is blended.

The blending amount of the compound represented by formula (1) of thepresent invention in each product is not strictly restricted and can bevariously changed according to use thereof. The blending amount of thecompound represented by formula (1) of the present invention in eachproduct is preferably from 0.0001 to 10% by mass, more preferably from0.001 to 5% by mass.

[Deodorant]

The compound represented by formula (1) of the present invention can beused, singly or in combination of two or more kinds, for a deodorant.

The deodorant of the present invention can be used after optionallyblending one kind or two or more kinds of known components selected froma cleaner, an antimicrobial, a fungicide, a deodorant, a naturalessential oil, a flavor or fragrance, an aroma material, a coolingsensation agent, a warming sensation agent, a rust inhibitor, anantifoaming agent, a pH adjusting agent, water, a solvent, a propellant,a surfactant, an insecticide, a repellent, an insect repellent, a waterrepellent, a degrading enzyme, an antistatic agent, a coloring matter,an ultraviolet absorber, a preservative, a chelating agent, anantioxidant, a thickener, a gellant, a water-absorbing resin, activatedcarbon, silica, a porous material, a resin, paper, felt, a higheralcohol, an inorganic salt, etc., and formulating the blend.

Examples of the known component include a cleaner such as alkylamineoxide, alkylamine, alkyl polyglycoside, naphthalenesulfonicacid-formalin condensate, hydrolyzed collagen peptide salt,acylmethyltaurine salt, N-acylamino acid salt, alkyl sulfate, ethercarboxylate, ether sulfonate, alkyltrimethylammonium chloride,dialkyltrimethylammonium chloride, alkylamine salt, alkyl amidopropylamino oxide, alkyl betaine, acetic acid betaine, fatty acid soap, etc.;an antimicrobial or fungicide such as 4-chloro-3,5-xylenol,isopropylmethylphenol, thymol, hinokitiol, phenol-based compound,polyphenol, catechin, tannin, natural product containing these, naturalproduct containing their derivative, etc.,2-(4′-thiazolyl)-benzimidazole, benzalkonium chloride, benzethoniumchloride, cetylpyridinium chloride, triclosan, silver ion, stabilizedchlorine dioxide, etc.; a deodorant such as lauryl methacrylate,methacrylate, geranyl crotonate, myristic acid acetophenone, glyoxal,abietic acid, flavonoid, polyphenol, plant extract, amphotericsurfactant, zinc ricinoleate, etc.; a natural essential oil such aslemon oil, orange oil, lime oil, bergamot oil, lavandin oil, lavenderoil, geranium oil, rose oil, sandalwood oil, etc.; a flavor orfragrance, for example, hydrocarbons such as α-pinene, β-pinene,limonene, p-cymene, thujone, etc., aliphatic alcohols such as octanol,p-tert-butylcyclohexanol, etc., terpene-based alcohols such as menthol,citronellol, geraniol, etc., aromatic alcohols such as benzyl alcohol,phenylethyl alcohol, etc., aliphatic aldehydes, terpene-based aldehydes,aromatic aldehydes, acetals, chain ketones, cyclic ketones such asdamascone, β-ionone, methylionone, etc., terpene-based ketones such ascarvone, menthone, isomenthone, camphor, etc., aromatic ketones such asacetophenone, raspberry ketone, etc., ethers such as dibenzyl ether,etc., oxides such as linalool oxide, rose oxide, etc., musks such ascyclopentadecanolide, cyclohexadecanolide, etc., lactones such asγ-nonalactone, γ-undecalactone, coumarin, etc., aliphatic esters such asacetic acid ester, propionic acid ester, etc., and aromatic esters suchas benzoic acid ester, phenylacetic acid ester, etc.; a compoundedflavor or fragrance prepared from the above-described natural essentialoil and flavor or fragrance; a powder flavor or fragrance of a knowncore-shell type, a matrix type using starch or processed starch, etc. ora fragrance capsule; a fragrance impregnated body prepared byimpregnating an inorganic porous material such as silica gel, calciumsilicate, etc., or an organic porous material such as celluloses, etc.,with a flavor or fragrance; a fragrance inclusion body prepared by theinclusion of a flavor or fragrance in α-cyclodextrin, β-cyclodextrin,γ-cyclodextrin, hydroxypropylated β-dextrin, highly branched cyclicdextrin, etc.; a known aroma material, for example, flavor or fragranceprecursor, pro-fragrance, fragrance precursor, pro-perfume, etc., suchas silicic acid ester compound, fatty acid ester compound, acetalcompound, hemiacetal compound, Schiff base compound, hemiaminalcompound, hydrazone compound, etc., which can release a flavor orfragrance component; a rust inhibitor such as trisodium citrate,ammonium citrate, sodium nitrite, ammonium benzoate, ammonium nitride,etc.; an antifoaming agent such as silicone, etc.; a pH adjusting agentsuch as citric acid, sodium monohydrogenphosphate, sodiumdihydrogenphosphate, potassium monohydrogenphosphate, potassiumdihydrogenphosphate, etc.; a solvent, for example, water, ethyl alcohol,propyl alcohol, isopropyl alcohol, butyl alcohol, modified alcohol,ethylene glycol, propylene glycol, dipropylene glycol, butylene glycol,pentylene glycol, hexylene glycol, polyethylene glycol, diethylphthalate, isopropyl myristate, triethyl citrate, benzyl benzoate,glycerin, triacetin, benzyl alcohol, paraffin, isoparaffin, a rosinester such as Hercolyn, etc., glycol ethers such as3-methoxy-3-methyl-1-butanol, ethyl carbitol (diethylene glycolmonoethyl ether), ethylene glycol monomethyl ether, propylene glycolmonomethyl ether, ethylene glycol monoethyl ether, dipropylene glycolmonomethyl ether, tripropylene glycol methyl ether, dipropylene glycoldimethyl ether, dipropylene glycol propyl ether, dipropylene glycolmethyl ether acetate, dipropylene glycol butyl ether, etc., a terpeneresin such as pinene polymer, etc., and silicones such as cyclicsilicone, etc.; a propellant, for example, a liquefied petroleum gassuch as propane, n-butane, isobutane, etc. a liquefied gas such asdimethyl ether, CFC (Chloro Fluoro Carbon), HCFC (Hydro Chloro FluoroCarbon), HFC (Hydro Fluoro Carbon), etc., and a compressed gas such asnitrogen, carbon dioxide, compressed air, nitrous oxide, etc.; and asurfactant such as polyoxyethylene alkyl ether,polyoxyethylene-polyoxypropylene copolymer, hydrogenated caster oil,sorbitan fatty acid ester, etc.

Examples of the formulated deodorant of the present invention includes adeodorizing mist, a deodorizing spray, a liquid deodorant, a geldeodorant, a solid deodorant, a sheet-shaped deodorant, a granulardeodorant, a beads deodorant, a powder deodorant, a smoke deodorant, adeodorant for toilet odor, a deodorant for urine odor, a deodorant forbody odor, a deodorant for sweat odor, a deodorant for foot odor, adeodorant for scalp odor, a deodorant for aging odor, a deodorant fornursing care, a deodorant for raw garbage odor, a fabric deodorizer, adeodorant for damp-dry odor, a deodorant for laundry care, a deodorantfor shoe cupboards, a shoe deodorizer, an entrance deodorizer, a roomdeodorizer, a bedroom deodorizer, a car freshener, a deodorant for drainodor, a deodorant for pets, a deodorant for diapers, a deodorant forclosets, a deodorant for air conditioners, etc.

The deodorant of the present invention can be used in a product such asaroma product, laundry care product, hair care product, cosmetic, oralcare product, hygiene product, insecticide, insect repellent,dehumidifying agent, cleaner, etc.

Examples of the aroma product include a liquid air freshener, a gel airfreshener, a powder air freshener, an impregnated air freshener, a beadsair freshener, a paper air freshener, a permeable film air fresher, aplug-type air freshener, a fan-type air freshener, an ultrasonic airfreshener, a water-absorbing polymer air freshener, a mist spray airfreshener, an aerosol spray air freshener, a plug-in air freshener, anincense stick, a candle, a reed diffuser, etc., in which a deodorizingfunction is imparted.

Examples of the laundry care product include a mist spray for clothing,a spray for clothing, a detergent, a fabric softener, an anti-wrinkleagent, etc., in which a deodorizing function is imparted.

Examples of the hair care product include a hair shampoo, a hair rinse,a hair conditioner, a hair treatment, a hair tonic, a hair stylingagent, a hair dye, a permanent waving agent, a hair growth agent, a hairlotion, a hair spray, etc., in which a deodorizing function is imparted.

Examples of the cosmetic include a lotion, a milky lotion, a cosmeticcream, a soap, a liquid soap, a facial cleanser, a sunscreen, anantiperspirant, a bath additive, a lipstick, a foundation, etc., inwhich a deodorizing function is imparted.

Examples of the oral care product include a toothpaste, a mouthwash, amouth spray, a mouth freshener, a denture care product, a breathfreshening product, etc., in which a deodorizing function is imparted.

Examples of the hygiene product include a paper diaper, a sanitaryproduct, wet tissue, tissue paper, toilet paper, a mask, etc., in whicha deodorizing function is imparted.

Examples of the cleaner include a toilet cleaner, a toilet bowl cleaner,a glass cleaner, a dishwashing detergent, a washing machine cleaner, adrain cleaner, a bathroom cleaner, a denture etc., in which adeodorizing function is imparted.

The blending amount of the compound represented by formula (1) of thepresent invention in each product is not strictly restricted and can bevariously changed according to use thereof. The blending amount of thecompound represented by formula (1) of the present invention in eachproduct is preferably from 0.0001 to 10% by mass, more preferably from0.001 to 5% by mass.

EXAMPLES

The present invention is hereunder specifically described by referenceto Examples, but it should be understood that the present invention isby no means limited by these Examples.

Test Example 1 (Example 1-1) Synthesis of2-isopropyl-5-methyl-1-cyclohexenyl Benzoate

To a mixed solution of (−)-menthone 4.63 g (30 mmol) and benzoicanhydride 2.26 g (10 mmol). p-toluenesulfonic acid monohydrate 95 mg(0.5 mmol) was added at room temperature, followed by stirring at 100 to110° C. (internal temperature) for 4.5 hours.

After cooling the reaction solution, the reaction was quenched by addingtoluene and water. The reaction solution was extracted with toluene, andthe organic layer was washed with a saturated sodium hydrogencarbonateaqueous solution and water. After drying the organic layer over sodiumsulfate, the filtrate was concentrated under reduced pressure to obtaina crude product. The resulting crude product was purified by silica gelcolumn chromatography to obtain 1.90 g of the target product.

(Example 1-2) Synthesis of 1,3-hexadienyl Benzoate

To a mixed solution of 2-hexenal 7.85 g (80 mmol), triethylamine 14.5 ml(104 mmol) and sodium benzoate 692 mg (4.8 mmol), benzoic anhydride 29.0g (128 mmol) was added at room temperature, followed by stirring at 115to 120° C. (internal temperature) for 8 hours.

After cooling the reaction solution, the reaction was quenched by addingtoluene and water. The reaction solution was extracted with toluene, andthe organic layer was washed with a saturated sodium hydrogencarbonateaqueous solution and water. After drying the organic layer over sodiumsulfate, the filtrate was concentrated under reduced pressure to obtaina crude product. The resulting crude product was purified by silica gelcolumn chromatography to obtain 13.26 g of the target product.

(Example 1-3) Synthesis of 3,7-dimethylocta-1,3,6-trienyl Benzoate

To a mixed solution of citral 1.52 g (10 mmol) and pyridine 3.15 ml (39mmol), benzoic anhydride 4.52 g (39 mmol) was added at room temperature,followed by stirring at 132 to 138° C. (internal temperature) for 7.5hours.

After cooling the reaction solution, the reaction was quenched by addingtoluene and water. The reaction solution was extracted with toluene, andthe organic layer was washed with 1 N hydrochloric acid, a saturatedsodium hydrogencarbonate aqueous solution and saturated brine. Afterdrying the organic layer over sodium sulfate, the filtrate wasconcentrated under reduced pressure to obtain a crude product. Theresulting crude product was purified by silica gel column chromatographyto obtain 1.60 g of the target product.

(Example 1-4) Synthesis of 3,7-dimethylocta-1,6-dienyl Benzoate

To a mixed solution of 1-citronellal 9.62 g (60 mmol), triethylamine10.9 ml (78 mmol) and sodium benzoate 519 mg (3.6 mmol), benzoicanhydride 21.7 g (96 mmol) was added at room temperature, followed bystirring at 112 to 118° C. (internal temperature) for 10 hours.

After cooling the reaction solution, the reaction was quenched by addingtoluene and water. The reaction solution was extracted with toluene, andthe organic layer was washed with a saturated sodium hydrogencarbonateaqueous solution and water. After drying the organic layer over sodiumsulfate, the filtrate was concentrated under reduced pressure to obtaina crude product. The resulting crude product was purified by silica gelcolumn chromatography to obtain 9.38 g of the target product.

(Example 1-5) Synthesis of 2,6-dimethylhepta-1,5-dienyl Benzoate

To a mixed solution of 2,6-dimethyl-5-heptenal 1.40 g (10 mmol),triethylamine 1.81 ml (13 mmol) and sodium benzoate 86 mg (0.6 mmol),benzoic anhydride 3.62 g (16 mmol) was added at room temperature,followed by stirring at 110 to 120° C. (internal temperature) for 10.5hours.

After cooling the reaction solution, the reaction was quenched by addingtoluene and water. The reaction solution was extracted with toluene, andthe organic layer was washed with a saturated sodium hydrogencarbonateaqueous solution and water. After drying the organic layer over sodiumsulfate, the filtrate was concentrated under reduced pressure to obtaina crude product. The resulting crude product was purified by silica gelcolumn chromatography to obtain 1.85 g of the target product.

Examples 1-6 to 1-9 Lipase-Induced Fragrance Emission Test:

10 mg of each of the compounds of Examples 1-1 to 1-3 and 1 g of anaqueous 1% lipase preparation solution were charged in a vial bottle andmixed and after hermetically sealing the bottle, the mixture wassubjected to GC/MS analysis of the head space component to obtain a peakarea of the fragrance emitting compound. As a control, water was used inplace of the aqueous 1% lipase preparation solution, and the peak areaof the control was obtained by the same method.

The fragrance emission amount was determined from the difference betweenthe peak area of the obtained fragrance emitting compound and the peakarea of the control. The results are shown in Table 1. As the lipasepreparation, Lipex 100L produced by Novozymes, and AY “Amano” 30SDproduced by Amano Enzyme Inc. were used.

(GC/MS Measurement Conditions)

Measuring apparatus: 7890GC/5975MSD (manufactured by AgilentTechnologies)

Column: BC-WAX 50 m×0.25 mm I.D.

Temperature rise: 70° C.→220° C., 4° C./min

Split ratio: 60:1

TABLE 1 Example 1-6 Example 1-7 Example 1-8 Example 1-9 CompoundCompound Compound Compound Compound of of of of Example 1-3 Example 1-1Example 1-2 Example 1-3 Fragrance 76,407,359 12,076,381 5,098,87016,031,669 emission amount Fragrance menthone hexenal citral citralemitting compound Lipase Lipex 100L AY “Amano” preparation 30SD

It was confirmed from the results of Table 1 that the compoundrepresented by formula (1) according to the present invention releasesan aromatic aldehyde or an aromatic ketone by the action of lipase andhas an effect as a flavor or fragrance precursor.

Examples 1-10 and 1-11

Test for Confirming Fragrance Emission from Hair at the Time of Use ofShampoo:

A shampoo was prepared according to a formulation shown in Table 2. Ahair bundle of 10 cm in length was cleaned using the prepared shampooand rinsed with tap water. After drying at room temperature for 15hours, about 0.3 g of an aqueous 1% lipase preparation solution wassprayed onto the hair bundle, and the scent on the hair bundle wassmelled to examine the presence or absence of fragrance emission fromhair. As the lipase preparation, AY “Amano” 30SD produced by AmanoEnzyme Inc. was used.

TABLE 2 Formulation of Shampoo Raw Material Example 1-10 Example 1-11Sodium 14 14 polyoxyethylenelaurylethersulfate Laurylsulfuric acidamidopropylbetaine 4 4 Coconut fatty acid diethanolamide 3 3 Cationizedcellulose 0.5 0.5 Ethylene glycol distearate 1 1 Paraoxybenzoic acidester 0.2 0.2 Compound of Example 1-4 0.3 — Compound of Example 1-5 —0.3 Deionized water 77 77 Total (% by mass) 100 100

It could be confirmed that citronellal emits a fragrance when lipase isallowed to act on the hair after drying, which was obtained using theshampoo prepared in Example 1-10.

It could be confirmed that 2,6-dimethyl-5-heptenal emits a fragrancewhen lipase is allowed to act on the hair after drying, which wasobtained using the shampoo prepared in Example 1-11.

Examples 1-12 and 1-13

Test for Confirming Fragrance Emission from Hair at the Time of Use ofHair Conditioner:

A hair conditioner was prepared according to a formulation shown inTable 3. A hair bundle of 10 cm in length was treated with the hairconditioner prepared and rinsed with tap water. After drying at roomtemperature for 15 hours, about 0.3 g of an aqueous 1% lipasepreparation solution was sprayed onto the hair bundle, and the scent onthe hair bundle was smelled to examine the presence or absence offragrance emission from hair. As the lipase preparation, AY “Amano” 30SDproduced by Amano Enzyme Inc. was used.

TABLE 3 Formulation of Hair Conditioner Raw Material Example 1-12Example 1-13 Stearyltrimethylammonium chloride 0.5 0.5Distearyldimethylammonium chloride 1.5 1.5 Cetanol 4.5 4.5Amino-modified silicone 0.5 0.5 Glycerin 5 5 Paraoxybenzoic acid ester0.2 0.2 Compound of Example 1-4 0.3 — Compound of Example 1-5 — 0.3Deionized water 87.5 87.5 Total (% by mass) 100 100

It could be confirmed that citronellal emits a fragrance when lipase isallowed to act on the hair after drying, which was obtained using thehair conditioner prepared in Example 1-12.

It could be confirmed that 2,6-dimethyl-5-heptenal emits a fragrancewhen lipase is allowed to act on the hair after drying, which wasobtained using the hair conditioner prepared in Example 1-13.

Examples 1-14 and 1-15

Test for Confirming Fragrance Emission from Towel at the Time of Use ofLiquid Detergent:

A liquid detergent was prepared according to a formulation shown inTable 4. A cotton towel was cleaned with the liquid detergent preparedand rinsed with tap water. After drying at room temperature for 15hours, about 0.3 g of an aqueous 1% lipase preparation solution wassprayed onto the towel, and the scent on the towel was smelled toexamine the presence or absence of fragrance emission from towel. As thelipase preparation, AY “Amano” 30SD produced by Amano Enzyme Inc. wasused.

TABLE 4 Formulation of Liquid Detergent Raw material Example 1-14Example 1-15 Polyoxyethylene alkyl ether 40 40 Straight chainalkylbenzenesulfonate 18 18 Butyl carbitol 10 10 Propylene glycol 3 3Monoethanolamine 3 3 Compound of Example 1-4 0.5 — Compound of Example1-5 — 0.5 Deionized water 25.5 25.5 Total (% by mass) 100 100

It could be confirmed that citronellal emits a fragrance when lipase isallowed to act on the towel after drying, which was obtained using theliquid detergent prepared in Example 1-14.

It could be confirmed that 2,6-dimethyl-5-heptenal emits a fragrancewhen lipase is allowed to act on the towel after drying, which wasobtained using the liquid detergent prepared in Example 1-15.

Examples 1-16 and 1-17

Test for Confirming Fragrance Emission from Towel at the Time of Use ofSoftener:

A softener was prepared according to a formulation shown in Table 5. Acotton towel was treated with the softener prepared and rinsed with tapwater. After drying at room temperature for 15 hours, about 0.3 g of anaqueous 1% lipase preparation solution was sprayed onto the towel, andthe scent on the towel was smelled to examine the presence or absence offragrance emission from towel. As the lipase preparation, AY “Amano”30SD produced by Amano Enzyme Inc. was used.

TABLE 5 Formulation of Softener Raw Material Example 1-16 Example 1-17Tri(oxyethylene)methylammonium 18 18 methylsulfate fatty acid esterPolyoxyethylene(23) lauryl ether 3 3 Propylene glycol 3 3 Calciumchloride 0.05 0.05 Compound of Example 1-4 0.5 — Compound of Example 1-5— 0.5 Deionized water 75.45 75.45 Total (% by mass) 100 100

It could be confirmed that citronellal emits a fragrance when lipase isallowed to act on the towel after drying, which was obtained using thesoftener prepared in Example 1-16.

It could be confirmed that 2,6-dimethyl-5-heptenal emits a fragrancewhen lipase is allowed to act on the towel after drying, which wasobtained using the softener prepared in Example 1-17.

Examples 1-18 and 1-19 and Comparative Example 1-1 Flavor or FragranceComposition:

A flavor or fragrance composition was prepared according to aformulation shown in Table 6.

TABLE 6 Formulation of Flavor or Fragrance Composition Example ExampleComparative Raw material 1-18 1-19 Example 1-1 Undecylene aldehyde 5 5 5Allylamyl glycolate 2 2 2 Allyl enanthate 5 5 5 Benzyl acetate 10 10 10Borneol 6 6 6 Cinnamic alcohol 7 7 7 Citronellol 50 50 50 Coumarin 3 3 3Tricyclodecenyl acetate 60 60 60 α-Damascone 1 1 1 Dihydromyrcenol 60 6060 Diphenyl oxide 3 3 3 Eucalyptus oil 1 1 1 Geraniol 30 30 30 Methyldihydrojasmonate 40 40 40 Hexyl cinnamic aldehyde 40 40 40 Lime oil 2525 25 Lemon oil 30 30 30 Linalol 80 80 80 Linalyl acetate 40 40 40 MUSKT (manufactured by 100 100 100 Takasago International Corporation,registered trademark) γ-Methylionone 20 20 20 Methyl nonyl ketone 2 2 2Nerol 20 20 20 ORBITONE (manufactured by 30 30 30 Takasago InternationalCorporation, registered trademark) 4-t-Butylcyclohexanol 30 30 30p-t-Butylcyclohexyl acetate 100 100 100 Compound synthesized in 200 — —Example 1-4 Compound synthesized in — 200 — Example 1-5 Dipropyleneglycol — — 200 Total (parts by mass) 1000 1000 1000

Examples 1-20 to 1-23 and Comparative Examples 1-2 to 1-5 LipaseDetergent/Softener Combination Use Test:

A liquid detergent in which lipase is blended or not blended wasprepared according to a formulation shown in Table 7. In addition, asoftener was prepared according to a formulation shown in Table 8. Asthe lipase preparation, Lipex 100L produced by Novozymes was used.

TABLE 7 Formulation of Liquid Detergent Blending of Non-Blending of RawMaterial Lipase Lipase Polyoxyethylene alkyl ether 40 40 Straight chainalkylbenzenesulfonate 18 18 Butyl carbitol 10 10 Propylene glycol 3 3Monoethanolamine 3 3 Lipase preparation/Lipex 100L 1 — Deionized water25 26 Total (% by mass) 100 100

TABLE 8 Formulation of Softener Example Example Comparative Raw material1-20 1-21 Example 1-2 Flavor or fragrance composition of 0.5 — — Example1-18 Flavor or fragrance composition of — 0.5 — Example 1-19 Flavor orfragrance composition of — — 0.5 Comparative Example 1-1Tri(oxyethylene)methylammonium 18 18 18 methylsulfate fatty acid esterPolyoxyethylene(23) lauryl ether 3 3 3 Propylene glycol 3 3 3 Calciumchloride 0.05 0.05 0.05 Citric acid 0.01 0.01 0.01 Sodium citrate 0.10.1 0.1 Deionized water 75.34 75.34 75.34 Total (% by mass) 100 100 100

Subsequently, a cotton towel was cleaned with the liquid detergentobtained above, and the cotton towel after cleaning was dehydrated andthen treated with the softener obtained above. After dehydration, thetowel was dried overnight. The fragrance intensity and fresh feeling ofthe towel during drying and after drying were evaluated by ten expertpanelists according to the following criteria. The evaluation score wasdetermined by averaging the evaluated values of the expert panelists.The results are shown in Table 9.

(Evaluation Criteria of Fragrance Intensity) 0: Odorless

1: Barely perceptible odor2: Weak odor can be seen in whether what of smell3: Odor easily perceivable4: Strong odor5: Intense odor

(Evaluation Criteria of Fresh Feeling)

0: No fresh feeling is sensed.1: Fresh feeling is lightly sensed.2: Fresh feeling is slightly sensed.3: Fresh feeling is sensed.4: Fresh feeling is fairly sensed.

TABLE 9 Fragrance Intensity and Fresh Feeling Example ComparativeExample Comparative Comparative 1-22 Example 1-3 1-23 Example 1-4Example 1-5 Liquid detergent blending of non-blending blending ofnon-blending blending of lipase of lipase lipase of lipase lipaseSoftener Example Example Example Example Comparative 1-20 1-20 1-21 1-21Example 1-2 Fragrance during 3.3 2.8 3.1 2.8 2.6 intensity drying after2.6 1.2 2.4 1.1 1 drying Fresh during 3.4 2.6 3.6 2.6 2.5 feeling dryingafter 2.8 0.6 3 0.7 0.5 drying

It could be confirmed that when a softener using a compounded flavor orfragrance having blended therein a compound represented by formula (1)of the present invention and a detergent having blended therein lipaseare used in combination, fragrance emission occurs and the fragranceintensity and fresh feeling after drying are enhanced.

Test Example 2 (Example 2-1) Synthesis of2-isopropyl-5-methyl-1-cyclohexenyl Benzoate

To a mixed solution of (−)-menthone 4.63 g (30 mmol) and benzoicanhydride 2.26 g (10 mmol), p-toluenesulfonic acid monohydrate 95 mg(0.5 mmol) was added at room temperature, followed by stirring at 100 to110° C. (internal temperature) for 4.5 hours.

After cooling the reaction solution, the reaction was quenched by addingtoluene and water. The reaction solution was extracted with toluene, andthe organic layer was washed with a saturated sodium hydrogencarbonateaqueous solution and water. After drying the organic layer over sodiumsulfate, the filtrate was concentrated under reduced pressure to obtaina crude product. The resulting crude product was purified by silica gelcolumn chromatography to obtain 1.90 g of the target product.

(Example 2-2) Synthesis of 1,3-hexadienyl Benzoate

To a mixed solution of 2-hexenal 7.85 g (80 mmol), triethylamine 14.5 ml(104 mmol) and sodium benzoate 692 mg (4.8 mmol), benzoic anhydride 29.0g (128 mmol) was added at room temperature, followed by stirring at 115to 120° C. (internal temperature) for 8 hours.

After cooling the reaction solution, the reaction was quenched by addingtoluene and water. The reaction solution was extracted with toluene, andthe organic layer was washed with a saturated sodium hydrogencarbonateaqueous solution and water. After drying the organic layer over sodiumsulfate, the filtrate was concentrated under reduced pressure to obtaina crude product. The resulting crude product was purified by silica gelcolumn chromatography to obtain 13.26 g of the target product.

(Example 2-3) Synthesis of 3,7-dimethylocta-1,6-dienyl Benzoate

To a mixed solution of 1-citronellal 9.62 g (60 mmol), triethylamine10.9 ml (78 mmol) and sodium benzoate 519 mg (3.6 mmol), benzoicanhydride 21.7 g (96 mmol) was added at room temperature, followed bystirring at 112 to 118° C. (internal temperature) for 10 hours.

After cooling the reaction solution, the reaction was quenched by addingtoluene and water. The reaction solution was extracted with toluene, andthe organic layer was washed with a saturated sodium hydrogencarbonateaqueous solution and water. After drying the organic layer over sodiumsulfate, the filtrate was concentrated under reduced pressure to obtaina crude product. The resulting crude product was purified by silica gelcolumn chromatography to obtain 9.38 g of the target product.

(Example 2-4) Synthesis of 2,6-dimethylhepta-1,5-dienyl Benzoate

To a mixed solution of 2,6-dimethyl-5-heptenal 1.40 g (10 mmol),triethylamine 1.81 ml (13 mmol) and sodium benzoate 86 mg (0.6 mmol),benzoic anhydride 3.62 g (16 mmol) was added at room temperature,followed by stirring at 110 to 120° C. (internal temperature) for 10.5hours.

After cooling the reaction solution, the reaction was quenched by addingtoluene and water. The reaction solution was extracted with toluene, andthe organic layer was washed with a saturated sodium hydrogencarbonateaqueous solution and water. After drying the organic layer over sodiumsulfate, the filtrate was concentrated under reduced pressure to obtaina crude product. The resulting crude product was purified by silica gelcolumn chromatography to obtain 1.85 g of the target product.

(Example 2-5) Synthesis of 3,5,5-trimethyl-1-hexenyl Benzoate

To a mixed solution of 3,5,5-trimethylhexanal 1.42 g (10 mmol),triethylamine 1.81 ml (13 mmol) and sodium benzoate 86 mg (0.6 mmol),benzoic anhydride 3.62 g (16 mmol) was added at room temperature,followed by stirring at 110 to 120° C. (internal temperature) for 7.5hours.

After cooling the reaction solution, the reaction was quenched by addingtoluene and water. The reaction solution was extracted with toluene, andthe organic layer was washed with a saturated sodium hydrogencarbonateaqueous solution and water. After drying the organic layer over sodiumsulfate, the filtrate was concentrated under reduced pressure to obtaina crude product. The resulting crude product was purified by silica gelcolumn chromatography to obtain 0.56 g of the target product.

(Example 2-6) Synthesis of 1-octenyl Benzoate

To a mixed solution of octanal 1.28 g (10 mmol), triethylamine 1.81 ml(13 mmol) and sodium benzoate 86 mg (0.6 mmol), benzoic anhydride 3.62 g(16 mmol) was added at room temperature, followed by stirring at 106 to119° C. (internal temperature) for 9.5 hours.

After cooling the reaction solution, the reaction was quenched by addingtoluene and water. The reaction solution was extracted with toluene, andthe organic layer was washed with a saturated sodium hydrogencarbonateaqueous solution and water. After drying the organic layer over sodiumsulfate, the filtrate was concentrated under reduced pressure to obtaina crude product. The resulting crude product was purified by silica gelcolumn chromatography to obtain 2.01 g of the target product.

(Examples 2-7 to 2-17) Deodorizing Component Emission Test byMicroorganism (Microorganism Culturing Method)

Culture of Staphylococcus aureus strain NBRC12732, Staphylococcusepidermidis strain JCM2414T, Corynebacterium xerosis strain JCM1324,Pseudomonas aeruginosa strain NBRC13275, Bacillus subtilis strainNBRC3134, and Moraxella osloensis strain

ATCC19976:

After inoculating each of bacteria in Muller-Hinton liquid medium,shaking culture was performed at 30° C. for 20 hours. 3 mL of theresulting preculture solution was transferred to a vial bottle, and 10mg of each of the compounds of Examples 2-2 to 2-6 was mixed, followedby hermetically sealing the bottle. Thereafter, shaking culture wasfurther performed at 30° C. for 20 hours.

Culture of Propionibacterium acnes Strain JCM6473:

After inoculating bacteria in GAM bouillon liquid medium containingHemin 0.5 ppm and Menadione 0.5 ppm, static culture was performed at 28°C. for 3 days under anaerobic conditions. 3 mL of the resultingpreculture solution was transferred to a vial bottle, and 10 mg of eachof the compounds of Examples 2-2 to 2-6 was mixed, followed byhermetically sealing the bottle. Thereafter, static culture was furtherperformed at 28° C. for 3 days.

Culture of Malassezia furfur Strain NBRC0656:

After inoculating bacteria in Sabouraud liquid medium containing 0.1%Tween 80, static culture was performed at 28° C. for 3 days underanaerobic conditions. 3 mL of the resulting preculture solution wastransferred to a vial bottle, and 10 mg of each of the compounds ofExamples 2-2 to 2-6 was mixed, followed by hermetically sealing thebottle. Thereafter, static culture was further performed at 28° C. for 3days.

(Test Method)

A peak area of the deodorizing compound was obtained by performing GC/MSanalysis of the head space component contained in the vial bottle having3 mL of microorganism culture solution in which 10 mg of each of thecompound of Examples 2-2 to 2-6 was mixed. A microorganism culturesolution having not mixed therein each of the compounds of Examples 2-2to 2-6 was used as the control, and a peak area of the control wasobtained by the same method as above.

The difference between the peak area of the deodorizing compound and thepeak area of the control was calculated as the deodorizing componentemission amount, and the results are shown in Tables 10 to 12.

(GC/MS Measurement Conditions)

Measuring apparatus: 7890GC/5975MSD (manufactured by AgilentTechnologies)

Column: BC-WAX 50 m×0.25 mm I.D.

Temperature rise: 70° C.→220° C., 4° C./min

Split ratio: splitless

TABLE 10 Deodorizing Component Emission Amount When Mixed withStaphylococcus aureus NBRC12732 Culture Solution Example 2-7 Example 2-8Example 2-9 Example 2-10 Compound Compound of Compound of Compound ofCompound of Example 2-3 Example 2-4 Example 2-5 Example 2-6 Deodorizingcitronellal 2,6-dimethyl-5- trimethylhexanal octanal component heptenalDeodorizing 1,064,240,572 132,554,000 189,916,125 129,928,279 componentemission amount

It was confirmed from the results of Table 10 that the compoundrepresented by formula (1) according to the present invention releases,as a deodorizing component, an aldehyde represented by formula (2) bythe action of Staphylococcus aureus.

TABLE 11 Deodorizing Component Emission Amount by Various Microorganismsfrom Compounds of Examples 2-2 and 2-3 Compound of Compound of CompoundExample 2-2 Example 2-3 Deodorizing component hexenal citronellalExample Staphylococcus epidermidis 17,179,106 76,886,509 2-11 JCM2414TExample Corynebacterium xerosis 15,168,728 692,091,257 2-12 JCM1324Example Pseudomonas aeruginosa 10,638,380 42,891,551 2-13 NBRC13275Example Bacillus subtilis 106,596,512 66,939,425 2-14 NBRC3134 ExampleMoraxella osloensis 8,864,491 25,608,586 2-15 ATCC19976 ExamplePropionibacterium acnes 3,265,759 15,450,553 2-16 JCM6473

It was confirmed from the results of Table 11 that the compoundrepresented by formula (1) according to the present invention releases,as a deodorizing component, an aldehyde represented by formula (2) bythe action of Staphylococcus epidermidis, Corynebacterium xerosis,Pseudomonas aeruginosa, Bacillus subtilis, Moraxella osloensis, orPropionibacterium acnes.

TABLE 12 Deodorizing Component Emission Amount When mixed withMalassezia furfur NBRC0656 Culture Solution Compound Compound of Example2-5 Deodorizing component trimethylhexanal Example 2-17 Malasseziafurfur 19,153,037

It was confirmed from the results of Table 12 that the compoundrepresented by formula (1) according to the present invention releases,as a deodorizing component, an aldehyde represented by formula (2) bythe action of Malassezia furfur.

(Examples 2-18 and Comparative Example 2-1) Deodorization Test on OdorEmitted from Microorganisms (Test Method)

A gauze impregnated with Triolein 1 g, Tricaproin 1 g and Androsterone0.5 g was set as a substrate in a petri dish of 33 mm in diameter ϕ.Furthermore, 1 mL of Staphylococcus aureus test bacterial solution(1×10⁹ cfu/mL) previously prepared in 0.9% physiological salinecontaining 0.2% L-leucine as a substrate was mixed with 3.5 μL of thecompound of Example 2-3, and the resulting mixture was uniformlyimpregnated into the gauze that was set. A cover was put on the petridish and after hermetically sealing it, culture was performed at 37° C.for 20 hours. The level of odor comfort/discomfort of the gauze afterculturing was sensorily evaluated by ten expert panelists according tothe following criteria. The evaluation score was determined by averagingthe evaluated values of the expert panelists.

In Comparative Example 2-1, evaluation was made on gauze subjected tothe same culturing without mixing the compound of Example 2-3. Theresults are shown in Table 13.

It is known that each of Triolein, Tricaproin, Androsterone andL-leucine emits malodor by the action of microorganisms.

(Evaluation Criteria of Level of Comfort/Discomfort)

+4: Extreme comfort

+3: great comfort

+2: comfort

+1: slight comfort

0: neither comfort nor discomfort

−1: slight discomfort

−2: discomfort

−3: great discomfort

−4: extreme discomfort

TABLE 13 Comparative Example 2-18 Example 2-1 Level of 1.5 −3.2comfort/discomfort

It was confirmed from the results of Table 13 that as shown byComparative Example 2-1, malodor was emitted along with proliferation ofStaphylococcus aureus under the test conditions above and the compoundrepresented by formula (1) can mitigate the malodor caused byStaphylococcus aureus.

Examples 2-19 and 2-20

A deodorizing mist was prepared according to a formulation shown inTable 14.

TABLE 14 Formulation of Deodorizing Mist Raw Material Example 2-19Example 2-20 Compound of Example 2-1 1 — Compound of Example 2-3 — 1Polyoxyethylene(60) hydrogenated 3 3 caster oil Deionized water 96 96Total (% by mass) 100 100

(Examples 2-21 and 2-22 and Comparative Examples 2-2 and 2-3)Deodorization Test on Worn Sock Odor by Deodorizing Mist (Test Method)

A cleaned right-foot sock made of man-made fiber was sprayed with 0.6 gof each of deodorizing mists obtained in Examples 2-19 and 2-20. InComparative Examples, a cleaned left-foot sock made of man-made fiber,which was not sprayed with deodorizing mist, was used. The level of odorcomfort/discomfort of the sock before wearing as well as after wearingfor 15 hours was sensorily evaluated by ten expert panelists accordingto criteria. As for the criteria, the criteria of Example 2-18 was used.The evaluation score was determined by averaging the evaluated values ofthe expert panelists. The results are shown in Table 15.

TABLE 15 Example 2-21 Example 2-22 (sprayed with (sprayed withdeodorizing mist deodorizing mist obtained in Comparative obtained inComparative Example 2-19) Example 2-2 Example 2-20) Example 2-3 Sockright foot left foot right foot left foot Level of before 0 0 0 0comfort/ wearing discomfort after 15 1.8 −2.2 1.5 −2 hours

In both of Example and Comparative Example, the sock before wearing wassubstantially odorless. The sock of Comparative Example after wearingfor 15 hours, which was not sprayed with the deodorizing mist of thepresent invention, emitted odor and caused discomfort, but in the stockof Example after wearing for 15 hours, which was sprayed with thedeodorizing mist of the present invention, offensive odor was notsensed. It could be confirmed that a deodorizing component is releasedfrom the compound represented by formula (1) and the unpleasantsensation is thereby alleviated.

Example 2-23

A deodorizing spray was prepared according to a formulation shown inTable 16.

TABLE 16 Formulation of Deodorizing Spray Raw Material Example 2-23Compound of Example 2-4 0.5 Ethanol 19.5 LPG 80 Total (% by mass) 100

(Example 2-24 and Comparative Example 2-4) Deodorization Test on SweatShirt by Deodorizing Spray (Test Method)

A sweaty shirt was prepared by wearing a cleaned cotton shirt andexercising vigorously. The shirt was put in a plastic bag and leftstanding at room temperature for 12 hours in a hermetically sealedstate. After taking out the shirt from the plastic bag, 1 g of thedeodorizing spray obtained in Example 2-23 was sprayed onto theright-side portion of the shirt. In Comparative Example, the deodorizingspray was not sprayed onto the left-side portion of the shirt.Thereafter, the shirt was left standing for 3 hours. The level of odorcomfort/discomfort in the right-side portion and left-side portion ofthe shirt was sensorily evaluated by ten expert panelists according tocriteria. As for the criteria, the criteria of Example 2-18 was used.The evaluation score was determined by averaging the evaluated values ofthe expert panelists. The results are shown in Table 17.

TABLE 17 Comparative Example 2-24 Example 2-4 Level of 1.4 −2.8comfort/discomfort

The left-side portion of the shirt not sprayed with the deodorizingspray of the present invention emitted odor and caused discomfort, butin the right-side portion of the shirt sprayed with the deodorizingspray of the present invention, offensive odor was not sensed. It couldbe confirmed that a deodorizing component is released from the compoundrepresented by formula (1) and the unpleasant sensation is therebyalleviated.

(Examples 2-25 to 2-27) Application Example to Deodorizing LiquidDetergent

A deodorizing liquid detergent was prepared according to a formulationshown in Table 18.

TABLE 18 Formulation of Deodorizing Liquid Detergent Example ExampleExample Raw Material 2-25 2-26 2-27 Polyoxyethylene alkyl ether 40 40 38Straight chain 18 18 18 alkylbenzenesulfonate Butyl carbitol 3 3 2Propylene glycol 3 3 4 Monoethanolamine 3 3 3 Flavor or fragrance 0.50.5 0.4 Compound of Example 2-4 0.5 — 0.3 Compound of Example 2-6 — 0.40.3 Deionized water 32 32.1 34 Total (% by mass) 100 100 100

(Examples 2-28 to 2-30) Application Example to Deodorizing Softener

A deodorizing softener was prepared according to a formulation shown inTable 19.

TABLE 19 Formulation of Deodorizing Softener Example Example Example Rawmaterial 2-28 2-29 2-30 Tri(oxyethylene)methylammonium 18 18 17methylsulfate fatty acid ester Polyoxyethylene(23) lauryl ether 3 3.5 4Propylene glycol 3 3 2 Calcium chloride 0.05 0.05 0.05 flavor orfragrance 0.8 1 0.8 Compound of Example 2-2 0.3 — 0.3 Compound ofExample 2-5 — 0.4 0.3 Deionized water 74.85 74.05 75.55 Total (% bymass) 100 100 100

While the invention has been described in detail and with reference tospecific embodiments thereof, it will be apparent to one skilled in theart that various changes and modifications can be made therein withoutdeparting from the spirit and scope of the invention. This applicationis based on Japanese Patent Application (Patent Application No.2017-007930) filed on Jan. 19, 2017 and Japanese Patent Application(Patent Application No. 2017-058118) filed on Mar. 23, 2017, thecontents of which are incorporated herein by way of reference.

INDUSTRIAL APPLICABILITY

Since the compound represented by formula (1) can release an aldehyde orketone that is a fragrance component by the action of a hydrolysate, thecompound can be used as a flavor or fragrance precursor and is useful.

By blending the compound represented by formula (1) according to thepresent invention in a flavor or fragrance composition or a product ofevery sort, the lingering fragrance having fresh feeling can be causedto last on the clothing, hair or skin, and the compound hasapplicability in the flavor or fragrance industry.

1. A method for releasing an aldehyde or ketone represented by formula(2) by allowing a hydrolase to act on a compound represented by formula(1), in which the compound represented by formula (1) is used as aflavor or fragrance precursor:

wherein in formula (1), each of R¹, R² and R³ independently represents ahydrogen atom, an alkyl group which may have a substituent, a cycloalkylgroup which may have a substituent, an alkenyl group which may have asubstituent, an aryl group which may have a substituent, or an aralkylgroup which may have a substituent, R¹ and R² or R¹ and R³ may form aring, and Ar represents an aryl group which may have a substituent, and:

wherein in formula (2), R¹, R² and R³ have the same definitions as thosein formula (1), and R¹ and R² or R¹ and R³ may form a ring.
 2. Themethod for releasing an aldehyde or a ketone according to claim 1,wherein the hydrolase is lipase.
 3. The method for releasing an aldehydeor a ketone according to claim 1, wherein each of R¹, R² and R³ isindependently a hydrogen atom, an alkyl group having 1 to 13 carbonatoms, which may have a substituent, or an alkenyl group having 2 to 13carbon atoms, which may have a substituent.
 4. A deodorizing methodincluding allowing a microorganism to act on a compound represented byformula (1) to release, as a deodorizing component, an aldehyde orketone represented by formula (2) and mitigating an odor caused bymicroorganism:

wherein in formula (1), each of R¹, R² and R³ independently represents ahydrogen atom, an alkyl group which may have a substituent, a cycloalkylgroup which may have a substituent, an alkenyl group which may have asubstituent, an aryl group which may have a substituent, or an aralkylgroup which may have a substituent, R¹ and R² or R¹ and R³ may form aring, and Ar represents an aryl group which may have a substituent, and:

wherein in formula (2), R¹, R² and R³ have the same definitions as thosein formula (1), and R¹ and R² or R¹ and R³ may form a ring.
 5. Thedeodorizing method according to claim 4, wherein the microorganism is atleast one selected from the group consisting of Staphylococcus bacteria,Corynebacterium bacteria, Propionibacterium bacteria, Pseudomonasbacteria, Bacillus bacteria, Moraxella bacteria, and Malassezia fungi.6. The deodorizing method according to claim 4, wherein each of R¹, R²and R³ is independently a hydrogen atom, an alkyl group having 1 to 13carbon atoms, which may have a substituent, or an alkenyl group having 2to 13 carbon atoms, which may have a substituent.
 7. A compoundrepresented by formula (3):

wherein in formula (3), a wavy line represents either one of E and Zgeometric isomers or a mixture thereof.
 8. A compound represented byformula (4):

wherein in formula (4), a wavy line represents either one of E and Zgeometric isomers or a mixture thereof.
 9. A flavor or fragrancecomposition containing a compound represented by formula (1):

wherein in formula (1), each of R¹, R² and R³ independently represents ahydrogen atom, an alkyl group which may have a substituent, a cycloalkylgroup which may have a substituent, an alkenyl group which may have asubstituent, an aryl group which may have a substituent, or an aralkylgroup which may have a substituent, R¹ and R² or R¹ and R³ may form aring, and Ar represents an aryl group which may have a substituent. 10.The flavor or fragrance composition according to claim 9, wherein eachof R¹, R² and R³ is independently a hydrogen atom, an alkyl group having1 to 13 carbon atoms, which may have a substituent, or an alkenyl grouphaving 2 to 13 carbon atoms, which may have a substituent.
 11. A flavoror fragrance composition containing the compound according to claim
 7.


12. A flavor or fragrance composition containing the compound accordingto claim
 8.


13. An aroma product, a laundry care product, a hair care product, acosmetic, a cleaner or a deodorant, containing a compound represented byformula (1):

wherein in formula (1), each of R¹, R² and R³ independently represents ahydrogen atom, an alkyl group which may have a substituent, a cycloalkylgroup which may have a substituent, an alkenyl group which may have asubstituent, an aryl group which may have a substituent, or an aralkylgroup which may have a substituent, R¹ and R² or R¹ and R³ may form aring, and Ar represents an aryl group which may have a substituent. 14.The aroma product, laundry care product, hair care product, cosmetic,cleaner or deodorant according to claim 13, wherein each of R¹, R² andR³ is independently a hydrogen atom, an alkyl group having 1 to 13carbon atoms, which may have a substituent, or an alkenyl group having 2to 13 carbon atoms, which may have a substituent.
 15. An aroma product,a laundry care product, a hair care product, a cosmetic, a cleaner or adeodorant, containing the compound according to claim
 7.


16. An aroma product, a laundry care product, a hair care product, acosmetic, a cleaner or a deodorant, containing the compound according toclaim 8,


17. An aroma product, a laundry care product, a hair care product, acosmetic, a cleaner or a deodorant, containing the flavor or fragrancecomposition according to claim
 9. 18. An aroma product, a laundry careproduct, a hair care product, a cosmetic, a cleaner or a deodorant,containing the flavor or fragrance composition according to claim 11.19. An aroma product, a laundry care product, a hair care product, acosmetic, a cleaner or a deodorant, containing the flavor or fragrancecomposition according to claim 12.